Water → HCID 18546789, compound

HRID 1634904Notes

Reaction equation

HRID 1634904 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=2)[N:5]=[CH:4][N:3]=1.[Se](=O)=[O:21].O>O1CCOCC1>[CH3:15][O:14][C:12]1[CH:13]=[C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([CH:1]=[O:21])[CH:7]=2)[CH:9]=[C:10]([O:18][CH3:19])[C:11]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 24007Selenium DioxideHCID 18546794HCID 18546794, compound

Product 1

HCID 18546789HCID 18546789, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

4-Methyl-6-(3,4,5-Trimethoxyphenyl)pyrimidine (920 mg) was dissolved in dioxane (100 mL), to the solution selenium dioxide (784 mg) was added, and the mixture was stirred overnight at 105° C. Water was added to the reaction mixture to conduct extraction with ethyl acetate, and the resultant organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound.

Workup

  1. additionwas added
  2. extractionextraction with ethyl acetate
  3. washthe resultant organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-25c04732804c4f2ca047d6a7ec9ffd25
Source dataset
uspto-grants-2003_01
Patent number
US06509329B1

Reaction notes

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